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Chemical Structure| 333432-28-3 Chemical Structure| 333432-28-3

Structure of 333432-28-3

Chemical Structure| 333432-28-3

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Product Details of [ 333432-28-3 ]

CAS No. :333432-28-3
Formula : C15H15BO2
M.W : 238.09
SMILES Code : CC1(C3=C(C2=CC=CC=C12)C=CC(=C3)B(O)O)C
MDL No. :MFCD08704227
InChI Key :DMDPAJOXRYGXCB-UHFFFAOYSA-N
Pubchem ID :22348454

Safety of [ 333432-28-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P305+P351+P338

Computational Chemistry of [ 333432-28-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 12
Fraction Csp3 0.2
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 74.21
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

40.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.33
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.67
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.28
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.86
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.83

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.84
Solubility 0.0343 mg/ml ; 0.000144 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.86
Solubility 0.0331 mg/ml ; 0.000139 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.85
Solubility 0.00339 mg/ml ; 0.0000142 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.39 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.7

Application In Synthesis of [ 333432-28-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 333432-28-3 ]

[ 333432-28-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 57103-20-5 ]
  • [ 333432-28-3 ]
  • 3,6-bis(9,9-dimethyl-2-fluorenyl)-9-phenylcarbazole [ No CAS ]
  • 2
  • [ 1698-16-4 ]
  • [ 333432-28-3 ]
  • C31H23N [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Reflux; 200mL of tetrahydrofuran is introduced into the compound B-1 14.8g (50mmol) synthesized in Production Example 5 and (9,9-dimethyl -9H- fluoren-2-yl) boronic acid (14.3g, 60mmol), followed by to this was added Pd (PPh3) 4 (2.89g, 2.5mmol) and 100mL2MK2CO3 aqueous solution, the resulting mixture was stirred for 12 hours while refluxing. The temperature was cooled to normal temperature and distilled water was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) was dried, then the solvent was removed, and subjected to silica gel column chromatography to give (39mmol, 78%) Compound 16.0g F-1.
  • 3
  • [ 160199-05-3 ]
  • [ 333432-28-3 ]
  • C45H29N3S [ No CAS ]
  • 4
  • [ 160199-05-3 ]
  • [ 333432-28-3 ]
  • C25H17ClN2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 3.0h;Reflux; 20.0 g (1.0 eq) of Compound A-1 (2,4-dichlorobenzo [4,5] thieno [3,2-d] pyrimidine), 9,9- 2-yl) boronic acid and tetrakis (triphenylphosphine) palladium (0) (Pd (PPh3) 4) (0.005 eq) was dissolved in 200 ml of tetrahydrofuran (THF), and 11.37 g (1.05 eq) of potassium carbonate (K2CO3) dissolved in water was added The mixture was refluxed and stirred. After 3 hours, the reaction was completed. After cooling, the aqueous layer was removed, and the organic solvent was removed by decompression. Then, it was completely dissolved in chloroform (CHCl3), washed with water, and further decompressed to remove about 50% of the solvent. Reflux phase Ethyl acetate was added to the crystals and the crystals were dropped and cooled. This was purified by column chromatography To obtain 23.95 g (yield: 74%) of intermediate 1
  • 5
  • [ 1000623-95-9 ]
  • [ 333432-28-3 ]
  • 3,6-bis(5-(9,9-dimethyl-9H-fluoren-2-yl)thiophen-2-yl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
37.5% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 100℃; for 24h;Inert atmosphere; <strong>[1000623-95-9]3,6-bis(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione</strong> (150.2mg, 0.22mmol) and 9,9-dimethylfluorene acid (157.2mg, 0.66mmol) was dissolved in toluene 15mL, 2mL aqueous sodium carbonate (sodium carbonate 186.5mg, 1.76mmol), After nitrogen gas was purged for 20 min, tetrakistriphenylphosphine palladium (10.2 mg, 0.0088 mmol) was added, and the mixture was heated to 100 C for 24 hours under nitrogen atmosphere, and then cooled to room temperature. Water and extracted three times with dichloromethane, the extract was dried over anhydrous magnesium sulfate, filtered to obtain the organic solution, the solvent was removed under reduced pressure, chromatographed on silica gel column with petroleum ether/ethyl acetate = 15:1 (v/v) as eluent, to give the crude product, then recrystallized from isopropanol, to give 75.1 mg of pure black product, a yield of 37.5%
 

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